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12806

Sigma-Aldrich

O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

≥97.0% (N), for peptide synthesis

Synonym(s):

N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate, TBTU

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About This Item

Linear Formula:
C11H16N5O · BF4
CAS Number:
125700-67-6
Molecular Weight:
321.08
Beilstein:
7066325
MDL number:
MFCD00077413
UNSPSC Code:
12352100
PubChem Substance ID:
329749883
NACRES:
NA.21

product name

O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate, ≥97.0% (N)

Quality Level

200

Assay

≥97.0% (N)

form

solid

mp

205 °C (dec.) (lit.)

solubility

acetonitrile: 0.1 g/mL, clear, colorless

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

F[B-](F)(F)F.CN(C)\C(On1nnc2ccccc12)=[N+](/C)C

InChI

1S/C11H16N5O.BF4/c1-14(2)11(15(3)4)17-16-10-8-6-5-7-9(10)12-13-16;2-1(3,4)5/h5-8H,1-4H3;/q+1;-1

InChI key

JKEKMBGUVUKMQB-UHFFFAOYSA-N

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Application

Coupling reagent which is ideally suited for solid-phase peptide synthesis.

Other Notes

Recent studies show that crystal as well as solution structure of this coupling agent is a guanidinium N-oxide and not an uronium compound; Coupling reagent which is ideally suited for solid-phase peptide synthesis.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H228,H317

Hazard Classifications

Flam. Sol. 1 - Skin Sens. 1A

Storage Class Code

4.1A - Other explosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBK6007
STBK5204
WXBD6643V
WXBD3762V
WXBC9203V

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Samer Al-Gharabli et al.
Materials (Basel, Switzerland), 11(5) (2018-05-08)
Advanced ceramic materials with a well-defined nano-architecture of their surfaces were formed by applying a two-step procedure. Firstly, a primary amine was docked on the ordered nanotubular ceramic surface via a silanization process. Subsequently, single-wall carbon nanotubes (SWCNTs) were covalently
S. Zimmer et al. et al.
Proc. 22nd Eur. Pept. Symp.: Peptides 1992 null
Parvin Zakeri-Milani et al.
EXCLI journal, 16, 650-662 (2017-07-12)
Gemcitabine (Gem) is used as a single agent or in combination with other anticancer agents to treat many types of solid tumors. However, it has many limitations such as a short plasma half-life, dose-limiting toxicities and drug resistance. Cell-penetrating peptides
O-(BENZOTRIAZOL-1-YL)-N, N, N', N'-TETRAMETHYLURONIUM TETRAFLUOROBORATE (TBTU): A NEW REAGENT FOR THE CLEAVAGE OF TETRAHYDROPYRANYL, SILYL AND 4, 4'-D IMETHOXYTRITYL ETHERS.
Ramasamy KS and Averett D.
Synlett, 6, 709-712 (1999)
Rajni Bala et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 196, 268-273 (2018-02-20)
In the present study, we report a highly sensitive, rapid and low cost colorimetric monitoring of malathion (an organophosphate insecticide) employing a basic hexapeptide, malathion specific aptamer (oligonucleotide) and silver nanoparticles (AgNPs) as a nanoprobe. AgNPs are made to interact
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Articles

Uronium and Guanidinium Salts

The special need of SPPS for rapid and highly efficient coupling reagents led to the development of several new reagents starting from BOP (Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate).

COMU-Safer and More Efficient Peptide Coupling Reagent

COMU is a non-explosive coupling agent suitable for solution phase & solid phase peptide synthesis. Its activity meets or exceeds that of HATU and its water-soluble by-product are easily removed.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

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